We’ve heard the story so many times. Some guy who’s good at “computers” drops out of college and goes on to become an incredibly successful CEO of a tech company. Yes that’s also the case with Anthony Casalena, Founder and CEO of Squarespace Inc. in New York City, but what you generally don’t hear is the story of a talented engineer who has to comes to terms with leaving behind directly making his own product to one who has to deal with running a company with hundreds of employees. I sit down with him to talk about his childhood influences, his favorite jacket, and why people even need websites in the first place.